Herbicidal composition and method of combating undesirable plant growth

ABSTRACT

Total herbicidal composition comprising a mixture of a dehalogenated benzonitrile or a derivative thereof, a halogenated aliphatic carboxylic acid and a triazine or a halogenated phenoxy-alkyl-carboxylic acid.

Unite States Patent HERBICIDAL COMPOSITION AND METHOD OF COMBATING UNDESIRABLE PLANT GROWTH 5 Claims, No Drawings U.S.Cl 71/93, 71/98, 71/105, 71/108,71/1 13,71/] 16 Int. Cl A0ln 9/22, AOln 9/12 Field 01 Search 71/105, 92,

[56] References Cited UNITED STATES PATENTS 3,318,681 5/1967 Yates 71/98 3,374,084 3/1968 Wijma et a1 71/98 X FOREIGN PATENTS 1,442,294 5/1966 France 71/92 1,067,032 4/1967 Great Britain 71/105 Primary Examiner-James 0. Thomas, Jr. Attorney-Frank R. Trifari I ABSTRACT: Total herbicidal composition comprising a mixture of a dehalogenated benzonitrile or a derivative thereof, a halogenated aliphatic carboxylic acid and a triazine or a halogenated phenoxy-alkyl-carboxylic acid.

HERBlClDAl, COMPOSITION AND METHOD OF COMBATING UNDESIRABLE PLANT GROWTH The present invention relates to a herbicidal composition and to the use thereof for controlling undesirable growth of plants.

For combating undesirable growth of plants. particularly. the annual and permanent weeds. various groups of herbicides are available. There may be mentioned halogenated phenoxyalkyl carboxylic acids, the salts or esters thereof. triazines. halogenated alkyl-carboxylic acids or dichlorobenzil or compounds converted into it when used in the soil. Ofthese groups of compounds especially. the following compounds have become known:

2.4-dichlorophenoxy-acetic acid or salts or esters thereof.

2.4.5-trichlorophenoxy-acetic acid or 2.4.S-trichlorophenoxy-propionic acid or salts or esters of these acids.

2-chloro-4-cthylamino-6-isopropylamino-s-triazine. 2-chloro-4.6-bisethylaminoJ-triazine. 2.2-dichloro-propionic acid. l.l.l-trichloro-acetic acid or the salts of the latter compounds.

2.6-dichloro-benzonitrile.

2.o-dichlorothiobenzamide.

N-hydroxymethyl-2.6-dichlorothiobenzamide.

The herbicidal activity of these compounds is different, which restricts on the one hand the practical usability of the separate compounds. but offers on the other hand the possibility of finding special uses or improving others by makin combinations of different active compounds.

it has been proposed to combine 2.fi-dichlorobenzonitrile with given halogenated phcnoxy-alkyl-earboxylic acids or salts thereof. it is also known to make combinations of 2.6- dichlorobenzonitrile generators, that is to say compounds converted in the soil into 2.6-dichlorobenzonitrile and given halogenated phenoxyalkyl-carboxylic acids. Generators of 2.6-dichlorobenzonitrile are. for example. N-hydroxymethyl- 2.6-dichlorothiobenzamide and 2.o-dichlorothiobenzamide.

As combinations there may be mentioned mixtures of 2.6- dichlorothiobenzamide or 2.6-dichlorobenzonitrile and an alkylor alkoxy-alkyhester of 2-methyl-4-chloro-phenoxyacetic acid or of y-2-methyl-4-chlorophenoxy-butyric acid (British Pat. specification No. 997.646). Furthermore there is known from Belgian Pat. specification No. 689.525 :1 mixture of 2.6-dichlorobenzonitrile (or a generator thereof) and the sodium salt of 2-(2.4-dichloro-phenoxy)-propionic acid. while in Japanese Pat. application No. 5559/67 21 herbicidal com-' position on the basis of 2-(2-methyl-4-chlorophenoxy)- propionic acid or a salt thereof and 2.6-dichlorobenzonitrile or a generator thereof is disclosed.

There is furthermore known 2.6-dichloro-4-hydroxybenzonitrile combined with 2.2'-dichloropropionic acid or a salt thereof (British Pat. specification No. 1.067.032). while there is further proposed to combine a salt of 2.2- dichloropropionic acid with 2-chloro-4-ethylamino-6- isopropyl-amino-s-triazine (atrazine) or with 2-chloro-4.6- ethylamino-s-triazine ("Chcm. Abstr." 54. 25.493 g. (1960)). There is furthermore known a herbicidal composition on the basis of 2-methyl-thio-4.6-bisisopropyl-amino-Z-triazine (prometrine). 2-(2-methyl-4'-chlorophcnoxy)-propionic acid of salts or esters thereof and 2.6-dichlorobenzonitrile or 2.6- dichlorothiohenzamide (Japanese Pat. specification No. 25.438/67).

Finally reference may be made to Pat. specification No. 39.l94 issued by the German Democratic Republic. in which a composition for weedkilling in potato cultures is disclosed to be used prior to the growth of the plants. said composition consisting of a mixture of 2-chloro-4.6-ethylamino-s-triazinc. 4.6-dinitro-o-crcsol. as the case may be. 4-chloro-2- methylphcnoxy-acetic acid. as the case may he. a.a'-dichloropropionic acid and. as the case may be. trichloro-acetic acid.

These known compositions are said to be suitable for combating given weeds in certain cultures or to be suitable for use as so-called "total weedkillers. that is to say. means capable of killing as far as possible all growth of plants on fallow land. along roads and railroads.

The invention relates to a composition for combating annual and permanent plants. which may be considered to be a total weedkiller." The compositions according to the invention are particularly suitable for combating deep-rooted weeds.

The particularlity of the composition according to the invention is that comparatively small quantities of the active substances are sufficient to achieve practically complete killing of given weeds. which cannot or can be hardly com:

bated by each of the separate components. Of these weeds there may be mentioned: Rammculus acris. iuxsilago farfara. Soncltus olcraceus. Urn'ca urens and Echium vulgare. Furthermore the composition according to the invention is particularly suitable for combating couch-grass (Agmpyron repens. Trilitum reports). I

The invention relates to a herbicidal mixture containing as active ingredients a mixture of a. one or more components ofthe general formula:

wherein X is a halogen atom. for example. Cl or Br and b. one or more halogenated aliphatic carboxylic acids or salts thereof having at the most four carbon atoms;

c. one or more triazlnes of the general formula wherein X is a chlorine or bromine atom or lower alkyl or alkenylgroup bonded with the triazine ring by sulfur or oxygen.

R is a lower alkyl-. alkenylor alkoxy-alkyl-group.

R, and R are hydrogen or a lower alkylor alkenyl-group and R is a lower alkoxy-alkyl-group and/or d. a halogenated phenoxy-alkyl-caroboxylic acid or a salt or an ester thereof.

Among the various compositions which are suitable in accordance with the invention. especially the following combinations provided very satisfactory results:

A. 2.6-dichlorobenzonitrile. 2,2-dichloropropionic acid in the form of the sodium salt. 2chloro-4-ethylamino-6- isopropylaminostriazinc;

B. N-hydroxymethyl-2.-dichlorothiobenzamide. 2.2- dichloro-propionic acid in the form of the sodium salt. 2.4.5- trichlorophenoxy-propionic acid in the form of the sodium salt;

C. 2.6-dichlorobenzonitrilc. trichloro-acetic acid. 2- chloro-4.fi-biscthylamino-s-trizaine;

D. 2.6-dichlorothiobenzamide. 2.2-dichloro-propionic acid. 2-chloro-4-ethylamino-(i-isopropylamino-s-triazine.

2.4.5-trichlorophenoxy-propionic acid in the form of the sodium salt.

The mixture of active ingredients may be processed in various ways to obtain compositions ready for use. such as dusts. miscible oils. but the active substances are preferably processed into granules. This may be achieved in a comparatively simple manner by mixing the active ingredients with wetting agents. absorption agents and carrier materials such as polyglycol, silicon dioxide and ground marmor. A further possibility consists in that granules of the individual active ingredients are produced and mixed with each other. This permits using separate techniques for producing granules of the From this table it is particularly apparent to what extent the effect of the composition according to the inveri tion is superioron grasses to the effect of the composition A containing two of the three active ingredients of compositions i various substances particularly suitable in respect of the spe- 5 In a further test composition A compared with comcial properties of the active'substances. For combating the P05ll10n(2)and Wllh afifth omp confalmng PF weeds the granules are preferably employed in doses of I00 to Gem of y P px f L000 kgs./hectar, while the active ingredients are contained l P i F' y y y 5- h in the granules by 0.5 to 5 percent. mide as active ingredients.

Particularly satisfying results have been obtained by 100 to lo The f of P n and grasses repeated three 400 kgs. of granules/hectar, which contained I to 2 percent of Wlth hese P doses were 400 E 2,6dichlorobenzonitri1e or N hydroxy'methy1 2.6 tar and the results were determined 2 months after the start 0 dichlorothiobenzamide or 2,-dichlorothiobenzamide, the treatment furthermore 2 to 5 percent of 2,2-dichloro-propionic acid (if I 5 TABLE II desired in the form of the sodium or potassium salt) or Total trichloro-acetic acid (if desire in the form of the sodium r 82? weight Weigh} Herbtcmal efiwp potassium salt) and I to 2 percent of 2-chloro-4-ethylamino-6- plants grasses plants, -71?! isopropylamino-s-triazine or 2-chloro-4,6-bisethylamino scomposition an S msses o triazine or 2 4,5-trichlorophenoxy-propionic acid (if desired Untreated 432 4612 23: 12( 1% 1% in the form of the potassium or sodium salt). A "$3 24 113 21 5 1 The invention will be described with reference to the fol- 123 184 307 23 34 I 118-,- 38 156 27 8 17 owing examples.

compnsmnns were made as mums: Also this tableshows the superior herbic dal effect of the l. o of Weight ompositions in accordance with the invention as compared a. 2.(t-dichltlrtt-bcllznnillilt: 1.0 with the effect of those containing only two of the active inb. 2,2-dichloro-pripionic acid g di (mum Sam In a third test the composition 1 was compared with comc. 2-chloro-4-cthylummo-6- is-u m iamitms tiultnc position A and with a sixth composltion (C) containing as an l/g y 3.0 active ingredient only 2, ;dichlorothiobenzamide in a quanti- "f ty of 7.5 percent. The latter composition also as a granule was L used in a dosis of 200 kg./hectar and the other compositions I001 were used in quantities of 400 kgsJhectar. The tests were car- 3 5 ried in duplicate and the results were determined 2 months /t by weight lateru. N-hydmxy-mcthyl-2,6- I

dichlnrothiobcnlamidc h. 2.2-dichloro-pripitmic acid TABLE i (sodium salt) Lt) Total c. 2,4.5-irichloropchnoxy-prupionic 40 Weight weight ac (potassium salt) 2.5 l gt Weight 1 ot Herbicldal eflect- Pll l pans grasses pans iif Q Composition in,g./rn in,g./m. g./m.' Plants Grasses Total dioxide) 20 326 @398" 724 100 100 100 Murmur dust 90.5 8, 181 71 152 25 18 21 lotto 565 97 152 17 m 21 43 s 51 13 2 7 '71 by weight H nut-u hi b I L I 0 Also these data show that the compos tion accord ng to the (sodium salt) L2 invention has considerably better herbicidal properties than a c. 2.4.s-trichloruph n xyp composition containing one or two of the active ingredients. z Especially the composition I has a very good effect on grasses.

ya y Micmsc, @(smmn dimidc M Ma further test the activity of composition I a number of Murmnr dust out specific weeds was examined. The activity of 2,6-

I 55 dichlorobenzonitrile, of 2.2-dichloro-propionic acid in the form of the sodium salt ands of 2-chloro-4-ethylamino-6- Th mposi ions mentioned under (1 (2) and w isopropylamino-s-triazine on these plants was determined for Produced y g lhe cofistlwems m a mixer until a compositions containing these substances as sole herbicides. hm'nogenofls 'f' Obmmedl as well as that of the combination of 2,6-dichlorobenzonitrile Table l indicates the average result of five different tes s with 2-chloro-4-ethylamino-6-isopropylamino-2-triazine. with a composition l and with a composition A containing 1 The results are indicated in the following table. percent of 2achloro-4-ethylamino-o-isopropylamino-2-triazine and 1 percent of 2,o-dichloro-benzonitrile and otherwise like TABLE composition I).

The two compositions were used in quantities of 400 5 kgsjhectan Th measurements were carried out 2 months Namcofthc weed 1710f killigg hytht:3 4 compositiosns after the application of the compositions to the plants.

TABLE I Ranunculux at-n's 40,! 0 0 I00 laruxaz'um vulgare 0 50 0 I00 weight g ggg 70 Malrl'trlrl'uimldom so so 0 I00 f w t of Hexbicidal ll lalrit'ariu c/Iammnilla 60 50 0 0 I00 Plants grasses plant I fa f u 50 i0 2o 0 0 mo Composition in,g./m. i1'i,g./m. gJm. Plants Grasses Total 0 Urlica arena 60 l() 0 0 I00 Xntreated" 32; gg Agmpymn repent 6O 4O 40 90 I00 1 71 19 18 2 75 Egl'um vulgurv l0 0 0 0 I00 anon The compositions 1 to 5 were made as follows:

I. Granule: content 1.5 percent of 2,6-dichlorobenzonitrile and 1.5 percent of 2-chloro-4-ethylamino-6-isopropylamino-striazine, quantities of 400 kgs./hectar;

2. Granule: content 7.5 percent of 2,6-dichlorobenzonitrile, quantities of 300 kgsJhectar;

3. Granule: content 4 percent of 2-chloro-4-ethylamino-6- isopropylamino-s-triazine, quantities of 250 kgsJhectar;

4. Aqueous solution of the sodium salt of 2,2- dichloropropionic acid containing kgs. of a substance of a purity of 85 percent;

5. Granule: content l percent of 2,G-dichloro-benzonitrile, 1 percent of 2-chloro-4-ethylamino-6-isopropylamin0-striazine, 2.5 percent of 2,2-dichloro-propionic acid in the form of the sodium salt, quantities of 100 kgs./hectar.

From the table there appears a nonpredictable synergistic activity of the constituents of the composition according to the invention.

What is claimed is:

l. A herbicidal composition comprising about 1 to 2 percent by weight of a member selected from the group consisting of 2,-dichlorobenzonitrile, N-hydroxy-methyl-2,6- dichlorothiobenzamide and 2,6-dlchlorothiobenzamide, about 2 to 5 percent by weight of a member selected from the group consisting of 2,2-dichloropropionic acid or a salt thereof and trichloroacetic acid or a salt thereof and about to 2 percent by weight of at least one member selected from the group consisting of 2-chloro-4-ethyl amin0-6-isopropylamino-s-triazine,

2-chloro-4,6-bisethylamino-5-triazine, and a trichlorophenoxy-alkane-carboxylic acid or a salt thereof and finely divided carriers therefore.

2. The herbicidal composition of claim 1, wherein there is present about 1 to 2 percent by weight of a member selected from the group consisting of 2,6-dichlorobenzonitrile. N- hydroxy-methyl-2,6-dichlorothiobenzamide and 2,6- dichlorothiobenzamide, about 2 to 5 percent by weight of a member consisting of 2,2-dichloropropionic acid, the sodium salt thereof and the potassium salt thereof and about I to 2 percent by weight of a member selected from the group consisting of 2-chloro-4-ethyl-amino-6-isopropylamino-s-triazine. 2-chloro-4,6-bisethylamino-S-triazine, 2,4,5-trichlorophenoxy-propionic acid, the potassium salt of said propionic acid and the sodium salt of said propionic acid.

3. The herbicidal composition of claim 1 wherein there is present 2,4,5-trichlorophenoxy-propionic acid, the potassium salt thereof or the sodium salt thereof.

4. The herbicidal composition of claim 1 wherein there is present a triazine selected from the group consisting of 2- chloro-4-ethyl-amino-6-isopropylamino-s-triazine and 2- chloro-4,6-bisethylamino-5-triazine.

5. The herbicidal composition of claim 1 wherein there is present a member selected from the group consisting of 2,2- dichloropropionic acid, the sodium salt thereof, the potassium salt thereof, trichloroacetic acid, the potassium salt thereof and the sodium salt thereof.

Patent No. 3, 28 ,943 Dated December 21', 1971 Bengt Hjalmar Gullfeldt Inventor(s) It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:

On the cover sheet insert [73] Assignee U. S. Philips Corporation, New York, N. Y.

Signed and sealed this 1st day of August 1972.

(SEAL) Attest: v g I EDWARD M. FLETCHER,JR. ROBERT GOTTSCHALK Attesting Officer Commissioner of Patents FORM PC4050 (10-69) USCOMM-DC 60376-P69 LL54 GOVERNMENT PRINTING OFFICE: 1959 0-366-334. 

2. The herbicidal composition of claim 1, wherein there is present about 1 to 2 percent by weight of a member selected from the group consisting of 2,6-dichlorobenzonitrile, N-hydroxy-methyl-2,6-dichlorothiobenzamide and 2,6-dichlorothiobenzamide, about 2 to 5 percent by weight of a member consisting of 2,2-dichloropropionic acid, the sodium salt thereof and the potassium salt thereof and about 1 to 2 percent by weight of a member selected from the group consisting of 2-chloro-4-ethyl-amino-6-isopropylamino-s-triazine, 2-chloro-4,6-bisethylamino-5-triazine, 2,4,5-trichlorophenoxy-propionic acid, the potassium salt of said propionic acid and the sodium salt of said propionic acid.
 3. The herbicidal composition of claim 1 wherein there is present 2,4,5-trichlorophenoxy-propionic acid, the potassium salt thereof or the sodium salt thereof.
 4. The herbicidal composition of claim 1 wherein there is present a triazine selected from the group consisting of 2-chloro-4-ethyl-amino-6-isopropylamino-s-triazine and 2-chloro-4, 6-bisethylamino-5-triazine.
 5. The herbicidal composition of claim 1 wherein there is present a member selected from the group consisting of 2,2-dichloropropionic acid, the sodium salt thereof, the potassium salt thereof, trichloroacetic acid, the potassium salt thereof and the sodium salt thereof. 